Potassium Hydroxide → HCID 12456487, compound

Participants

Reaction Steps

To a solution of diethyl 2-hexylmalonate of Example 8 (244.36 g, 1.000 mol) in 25 mL of absolute ethanol in a 2-L, 3-necked Morton flask was added a solution of potassium hydroxide (59.9 g, 0.907 mol)(weight adjusted for 85% assay of commercial potassium hydroxide) in 450 mL of absolute ethanol dropwise via a 500-mL pressure-equalizing dropping funnel over 75 min. The funnel was washed with 25 mL of absolute ethanol. The reaction mixture was stirred for 2 h, and 300 mL of ethanol was then removed under reduced pressure. Water (500 mL) was added, and the mixture extracted with 500 mL of heptane to remove unreacted diethyl 2-hexylmalonate. The aqueous solution was acidified with 12 M HCl to pH 2 then extracted with 500 mL of heptane. The heptane solution was dried (MgSO4) and the solvent removed under reduced pressure to give 2-(ethoxycarbonyl)octanoic acid as a colorless oil. Traces of ethanol were removed by adding 20 mL of toluene to the crude product, followed by stripping of the solvent at 1 mm Hg of pressure with stirring. The yield was 190.9 g (0.8827 mol, 88.3% based on diethyl 2-hexylmalonate, 97% based on potassium hydroxide).

Provenance & Evidence